Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
1999-02-26
2002-01-22
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S407000, C008S423000, C008S571000, C008S573000, C548S154000, C548S165000
Reexamination Certificate
active
06340372
ABSTRACT:
The subject-matter of the invention is a composition for the oxidation dyeing of keratinous fibres, in particular human keratinous fibres, such as hair, comprising, as coupler, at least one thiazoloazole S-oxide compound and/or at least one thiazoloazole S,S-dioxide compound and at least one oxidation base.
It is known to dye keratinous fibres and in particular human hair with dyeing compositons comprising oxidation dye precursors, in particular ortho- or para-phenylenediamines, ortho- or para-aminophenols, or heterocyclic compounds, generally known as oxidation bases. Oxidation dye precursors or oxidation bases are colourless or weakly coloured compounds which, in combination with oxidizing products, can give rise, by an oxidative coupling process, to coloured and colouring compounds.
It is also known that it is possible to vary the shades obtained with these oxidation bases by combining them with couplers or colouring modifers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds, such as indole compounds.
The variety of the molecules involved as oxidation bases and couplers makes it possible to obtain a rich palette of colours.
The so-called “permanent” colouring obtained by virtue of these oxidation dyes has, however, to satisfy a certain number of requirements. Thus, it must be without disadvantage toxicologically and it must make it possible to obtain shades with the desired intensity and behave well in the face of external agents (light, bad weather, washing, permanent waving, perspiration or rubbing).
The dyes must also make it possible to cover white hair and, finally, be as non-selective as possible, that is to say make it possible to obtain the smallest possible differences in colouring along the same keratinous fibre, which can in fact be differently sensitized (i.e. damaged) between its tips and its root.
The Applicant Company has not just discovered that it is possible to obtain powerful novel dyes, which are not very selective, which are particularly resistant and which are capable of generating intense colourings in varying shades, by using, as couplers, thiazoloazole S-oxide and/or thiazoloazole S,S-dioxide compounds in the presence of an oxidation base.
This discovery forms the basis of the present invention.
The subject-matter of the invention is a composition for the oxidation dyeing of keratinous fibres and in particular of human keratinous fibres, such as hair, charactierized in that it comprises, in a medium appripriate for dyeing:
as coupler, at least one thiazoloazole S-oxide compound and/or at least one thiazoloazole S,S-dioxide compound of formula (I) and/or at least one of their addition salts with an acid:
in which:
R
1
represents a hydrogen atom; a halogen atom, such as bromine, chlorine or fluorine; an alkoxy radical (such as, for example: methoxy, ethoxy, propyloxy, benzyloxy, methoxyethoxy, phenoxyethoxy, 2-cyanoethoxy, phenethyloxy, p-chlorobenzyloxy or methoxyethylcarbamoylmethoxy); an aryloxy radical (such as, for example: phenoxy, 4-methoxyphenoxy, 4-nitrophenoxy, 4-cyanophenoxy, 4-methanesulphonamidophenoxy, 4-methanesulphonylphenoxy, 3-methylphenoxy or 1-naphthyloxy); an acyloxy radical (such as, for example: acetoxy, propanoyloxy, benzoyloxy, 2,4-dichlorobenzoyloxy, ethyoxyoxaloyloxy, pyruvoyloxy, cinnamoyloxy or myristoyloxy); an arylthio radical (such as, for example: phenylthio, 4-carboxyphenylthio, 2-ethoxy-5-tert-butylphenylthio, 2-carboxyphenylthio or 4-methanesulphonylphenylthio); an alkylthio radical (such as, for example: methylthio, ethylthio, propylthio, butylthio, 2-cyanoethylthio, benzylthio, phenethylthio, 2-(diethylamino)ethylthio, ethyoxyethylthio or phenoxyethylthio); a heteroarylthio radical (such as, for example: 5-phenyl-2,3,4,5-tetrazolythio or 2-benzothiazolylthio); a heteroaryloxy radical (such as, for example: 5-phenyl-2,3,4,5-tetrazolyloxy or 2-benzothiazolyloxy); a thiocyano radical; an alkyloxythiocarbonylthio radical (such as dodecyloxythiocarbonylthio); a sulphonamido radical (such as benzenesulphonamido or N-ethyltoluenesulphonamido); a pentafluorobutanamido radical; a 2,3,4,5,6-pentafluorobenzamido radical; a pyrazolyl radical; an imidazolyl radical; a triazolyl radical; a tetrazolyl radical; a benzimidazolyl radical; a 1-benzyl-5-ethoxy-3-hydantoinyl radical; a 1-benzyl-3-hydantoinyl radical; a 5,5-dimethyl-2,4-dioxo-3-oxazolidinyl radical; a 2-oxo-1,2-dihydro-1-pyridinyl radical; an alkylamido radical; an arylamido radical; an NR
III
R
IV
radical with R
III
and R
IV
, which are identical or different, representing a C
1
-C
4
alkyl or a C
1
-C
4
hydroxyalkyl; a carboxyl radical; an alkoxycarbonyl radical; an alkyloxycarbonylamino radical; an aryloxcarbonylamino radical; a sulphonyloxy radical, such as methanesulphonyloxy; an alkoxycarbonyloxy radical, such as methoxycarbonyloxy or ethoxycarbonyloxy; or an aryloxycarbonyloxy radical, such as phenyloxycarbonyloxy;
Z
a
, Z
b
and Z
c
represent, independently of one another, a nitrogen atom or else a carbon atom carrying an R
2
, R
3
or R
4
radical; provided that:
when Z
a
denotes a carbon atom carrying an R
2
radical, then Z
b
represents a nitrogen atom and Z
c
denotes a carbon atom carrying an R
3
radical;
when Z
a
denotes a nitrogen atom, then Z
b
represents a carbon atom carrying an R
4
radical and Z
c
denotes a nitrogen atom;
R
2
, R
3
and R
4
represent, independently of one another, a hydrogen atom; a linear or branched C
1
-C
20
alkyl radical optionally substituted by 1 or 2 R radicals chosen from the group consisting of halogen, nitro, cyano, hydroxyl, alkoxy, aryloxy, amino, alkylamino, acylamino, carbamoyl, sulphonamido, sulphamoyl, imido, alkylthio, arylthio, aryl, alkoxycarbonyl or acyl; an aryl radical (such as phenyl or naphthyl) optionally subsititued by 1 or 2 R radicals as defined above; a halogen atom (such as bromine, chlorine or fluorine); an acyl radical; a sulphonyl radical; a sulphinyl radical; a phosphonyl radical; a carbamoyl radical; a sulphamoyl radical; a cyano radical; an amino radical; an alkylamino radical; an acylamino radical; an alkylthio radical; an arylthio radical; an acyloxy radical; a carbamoyloxy radical; a sulphonamido radical; an imido radical; a uredido radical; a sulphamoylamino radical; an alkoxycarbonylamino radical; an aryloxycarbonylamino radical; an alkoxycarbonyl radical; an aryloxycarbonyl radical; a carboxyl radical; a nitro radical; a sulphonyl radical; a hydroxyl radical; a mercapto radical; or a trifluoromethyl radical;
n has the value 1 or 2;
and at least one oxidation base.
The addition salts with an acid of the compounds of the invention can be chosen in particular from hydrochlorides, hydrobromides, tartrates, tosylates, benzenesulphonates, sulphates, lactates and acetates.
Preference is given, among the R
1
radicals of the formula (I) defined above, to the radicals chosen from the group consisting of a hydrogen atom; a C
1
-C
4
alkoxy radical; a phenoxy radical; a phenoxy radical substituted by a halogen atom, a C
1
-C
4
alkyl, a carboxyl, a trifluromethyl group or an acyloxy, benzyloxy or C
1
-C
4
alkylthio radical; a phenylthio radical; a phenylthio radical substituted by a halogen atom, a C
1
-C
4
alkyl, a carboxyl or a trifluoromethyl group; a C
1
-C
4
alkylamido radical; a phenylamido radical; an NR
III
R
IV
radical with R
III
and R
IV
, which are identical or different, representing a C
1
-C
4
alkyl or a C
1
-C
4
hydroxyalkyl; a carboxyl radical; a C
1
-C
4
alkoxycarbonyl radical or a halogen atom, such as chlorine or bromine.
More particularly still, preference is given to the R
1
radicals chosen from the group consisting of hydrogen, chlorine, ethoxy, phenoxy, benzyloxy, acyloxy, acetamido and dimethylamino.
Preference is given, among the R
2
, R
3
or R
4
radicals of the formula (I), to the radicals chosen from the group consisting of a hydrogen atom; a linear or branched C
1
-C
4
alkyl radical; an aryl radical; an aryl radical substituted by a halogen atom, a methoxy radical
Malle Gerard
Vidal Laurent
Einsmann Margaret
L'Oreal (S.A.)
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